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Merck
CN

N2286

无活菌素

from Streptomyces griseus, ≥98.0% (Total homologs, HPLC)

别名:

铵离子载体

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关于此项目

经验公式（希尔记法）:
C40H64O12
化学文摘社编号:
6833-84-7
分子量:
736.93
NACRES:
NA.76
PubChem Substance ID:
24897566
UNSPSC Code:
51102829
EC Number:
229-911-3
Beilstein/REAXYS Number:
76434

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产品名称

无活菌素, from Streptomyces griseus, ≥98.0% (Total homologs, HPLC)

InChI

1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-

InChI key

RMIXHJPMNBXMBU-QIIXEHPYSA-N

SMILES string

C[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](C)C[C@H]3CC[C@H](O3)[C@H](C)C(=O)O[C@@H](C)C[C@@H]4CC[C@@H](O4)[C@@H](C)C(=O)O[C@H](C)C[C@H]5CC[C@H](O5)[C@H](C)C(=O)O1

biological source

Streptomyces griseus

description

Natural macrotetrolide, may contain homologues (like monactin and dinactin)

assay

≥98.0% (Total homologs, HPLC)

form

powder

solubility

chloroform: soluble 10 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes
cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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相关类别

Application

Nonactin is a macrotetrolide that forms complexes with alkali cations, such as potassium and sodium. Nonactin has been reported to inhibit the processing of cytoplasmic precursor proteins destined for the mitochondria. Nonactin is an uncoupler of oxidative phosphorylation .

Biochem/physiol Actions

Nonactin is used as a neutral lipid membrane soluble ammonium (and potassium) ionophore, and to inhibit surface expression of certain heat shock proteins (HSP60) .

General description

Chemical structure: macrolide

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

涉药品监管产品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000486074
0000486074
0000473187
0000473187
0000458712

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Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
ChemInform, 52, 571-571 (1996)
Pei-Ji Zhao et al.
Archives of pharmacal research, 28(11), 1228-1232 (2005-12-15)
Four compounds, including two novel macrolides, were isolated from an endophyte Streptomyces sp. Is9131 of Maytenus hookeri. Spectral data indicated that these compounds were dimeric dinactin (1), dimeric nonactin (2), cyclo-homononactic acid (3), and cyclo-nonactic acid (4). Bioassay results showed
Brian R Kusche et al.
Journal of the American Chemical Society, 131(47), 17155-17165 (2009-11-12)
Nonactin is a polyketide antibiotic produced by Streptomyces griseus ETH A7796 and is an ionophore that is selective for K(+) ions. It is a cyclic tetraester generated from two monomers of (+)-nonactic acid and two of (-)-nonactic acid, arranged (+)-(-)-(+)-(-)
V Gh Shlyonsky et al.
Biochimica et biophysica acta, 1758(11), 1723-1731 (2006-10-31)
We describe the phenomenon of mechanoelectrical transduction in macroscopic lipid bilayer membranes modified by two cation-selective ionophores, valinomycin and nonactin. We found that bulging these membranes, while maintaining the membrane tension constant, produced a marked supralinear increase in specific carrier-mediated
Brian R Kusche et al.
Bioorganic & medicinal chemistry letters, 19(4), 1233-1235 (2009-01-27)
Nonactin, produced by Streptomyces griseus ETH A7796, is a macrotetrolide assembled from nonactic acid. It is an effective inhibitor of drug efflux in multidrug resistant erythroleukemia K562 cells at sub-toxic concentrations and has been shown to possess both antibacterial and
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